Caffeinated Chaos

46. From Military Service to CEO: How Systems Gave Purpose and Built His Business with Guest Jay Jackson

• Whitney Aguon • Episode 46

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In this powerful episode, Whitney sits down with a former Air Force veteran turned systems strategist and business coach who opens up about his journey from military service to entrepreneurship. After being laid off during a Department of Defense downsizing, he faced bankruptcy, lost his home and custody of his kids, and had to reinvent himself from the ground up. Now, he helps coaches, thought leaders, and experts build smart systems that bring in consistent leads and sales—without the burnout.

What You’ll Learn in This Episode:

  • What it’s really like to start over after military service
  • How personal setbacks can lead to massive breakthroughs
  • Why systems are the secret weapon of successful entrepreneurs
  • The mindset shift from employee to CEO
  • How serving others became his purpose-driven business model

Connect With Jay:



Cheers! Thank you for joining us for another episode. Have a chaotic moment, question, or topic you want us to cover? Drop us a message or leave a review! If you loved this episode, share it with a friend who thrives in beautiful chaos too.

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The views and opinions expressed by guests on Caffeinated Chaos are their own and do not necessarily reflect the views, beliefs, or positions of Whitney Aguon or Aguon Studios LLC. The content shared by guests is for informational and entertainment purposes only. We encourage listeners to do their own research and form their own...

Welcome to Caffeinated Chaos, where business deals happen between diaper changes and friendships are fueled by caffeine. I'm Whitney GaN, your host, and I'm here to talk all things business parenthood, and of course keeping up with the BFFs, whether you're juggling the boardroom, the playroom, or just here for some coffee fuel chaos. We've got you covered. Get ready for real talk, laughs and a whole lot of heart as we dive into the beautiful mess that is entrepreneurship, parenthood, and everything in between. So let's embrace the chaos together. Ated, of course. I am excited to introduce today's guest, Jay Jackson. Jay is a transformational leader, business strategist, and systems expert who went from an overworked and underpaid to building a life of freedom, working just five hours a day while helping others elevate their impact, income, and authority. He's the creator of the catalyst system and a master at making success simple, sustainable, and purpose driven. Get ready.'cause this conversation is packed with wisdom you do not wanna miss. Grab those cups of coffee, find a comfy spot, and let's welcome Jay to the podcast. Welcome to the podcast, Jay. How are you doing today? I'm doing outstanding. Thank you for having me on. Yeah. Oh my gosh, I'm so excited. Listeners, we talked a little bit before we started hitting record, and Jay and I have so many parallels going on with like locations we've been in, places we've lived that it's awesome. I can't wait to get started. But first, before I get too far into it, Jay, why don't you tell our listeners a little bit about yourself? Yeah, well, I'm probably like most of your listeners, just a guy who loves family and, you know, things that I'm passionate about in terms of serving and helping people. Mm-hmm. I'm a young little country boy, is what I like to tell people from, originally from Birmingham, Alabama. You probably can't tell, by the way that I talk, but every now and then a little twang might fall out. But I am a military brat. My stepfather was in the Navy, and so we traveled across this country Before graduating high school, I had lived in seven different states. Wow. Then I guess I was a glutton for, uh, chaos and, instability so much that I turned around and joined the Air Force and did 15 years in the Air Force myself. And so I lived in multiple countries, visited multiple countries, loved everything about it. But, and unfortunately, like most people, whenever a major corporation does a downsizing, in this case, the Department of Defense cut 250,000 people back in 2014, and unfortunately, I was one of those 250,000, and so I had to find my next opportunity. I was pretty devastated when this happened because of course, you know, you put your life on the line for something literally that mm-hmm. Believed in, uh, only for it to say, Hey, your service no, are no longer wanted. So it was pretty devastating for me. A lot of PTSD, chaos, as I'm sure we're gonna talk, you know, about here shortly. Yeah. Just completely, you know, changed my life but I'm grateful I. I'm grateful for the entire experience because now looking back, I wouldn't be able to have amazing conversations like this with you. Mm-hmm. Or meet some of the amazing people that I've been able to meet and do some of the cool things that I've been able to do. So, kind of in a, in a nutshell, that's me. But I'm sure we'll unpack a lot of that a little bit as we get into our conversation. Now you are an entrepreneur. Yeah. And so you work with leaders in the industry, right? Specifically just helping coaches, thought leaders and experts, create a system so that they can get leads and sales consistently, uh, to work less in their business while profiting more, because obviously we started our businesses. Mm-hmm. So we can have time and financial freedom. Not that we're, you know, stuck in the trenches, you know, dealing with technology and all the things that, you know, we struggle with when it comes to building an online business. I've basically been able to crack several of the codes and so now I just go back and I teach and help people avoid the mistakes or, the waste of time or even the waste of money. Yeah. They don't have to go through the same process that I went through. Oh, I love that. I am a systems girl through and through. I love it. See another pill. I love this. This is gonna be cool. Yeah, it's gonna be cool. I love systems. I feel like ever since, I don't know, maybe. High school, college. I just like, I just love tinkering with stuff too, and, and trying to figure it out. And it's so awesome that you're helping other people. My listeners probably know this story like a hundred percent already, but like my life skills teacher back in high school, she always taught us that like as we rose to reach back and pull someone up with us. And so I love the fact that like. Your business and the way that you are is helping those to also, you know, like you said, have more freedom, not so much of the headache of trying to figure out the backend system by implementing what you already know and teaching it to the next generation or the next. A wave of entrepreneurs for sure. Yeah. It's just like I've always had the mentality of service, right? Yeah. So growing up in church as a young kid, I told you I was a Navy brat, so that's, we served, I joined the Air Force Service and so I. It was, for me, it was, it's, I almost, it's innate or deeply, you know, programmed or conditioned into me to serve and help people. And so I just try to be what I wish I had. Right? Yeah. And so I think sometimes we miss out on, what I think is our purpose, our mission or our calling, because we just sometimes, fail to realize how powerful our own experiences are. When it comes to being able to serve and help other people. And so, I tell people all the time, it's very selfish. So if I do something for you and it makes you feel good, like Bravo, but I promise you I didn't really do it to make you feel good. I did it to, it makes me feel really good to, to help people, to help see people smile or to not have to, you know, be stressed or frustrated or anything like that. That fuels me, that, that lights me up inside. I kind of geek out on it. I love that. It's very much a win-win for the both of you too. Hundred percent. Did you start this because of the layoffs and then you had to pivot to find, or was it like you did something else and then eventually you had this aha moment? Yeah, yeah, yeah. When I first transitioned out, my plan was to start an upscale lounge. I was, oh, okay. Yeah. I was in middle Georgia, which is where I got outta the Air Force at. And in that particular area, while I was in the Air Force, we would have to either drive to Atlanta hour and a half drive. And then of course if you, were brave enough soul to have a few beverages and drive back, you'd drive an hour and a half back. Sometimes we would spend the night in Atlanta, but then after a while, I became a full-time single dad after going through my divorce. A lot of the. Friends we were single and some of them were single moms and single dads as well. And so it was just like, Hey, it's impossible for us to keep traveling to Atlanta. Oh, yeah. Getting a hotel room and then now we have to find childcare, but we're all friends, so how do we, like who's gonna watch our kids if we're all trying to go up and party and have a good time? Yeah, exactly. What we started to do is I started to do like an open mic night on base. And it was amazing. Like everyone loved it because you didn't have to travel to the city to have a good time. That's so cool. And still, you know, have date nights and things like that. And so when I got out, the plan was to start this upscale lounge'cause there wasn't one there. But I was very, naive in my understanding around exactly how much capital I would need in order to start it, and then what it would take to actually operate it. Like, yes, I could get people in the door and I had proven that with like the open mic night, and I could keep a crowd, you know, excited the entire time. But the overhead expenses of, you know, one, getting a place built out and retrofitted for, food costs, liquor license, all the things. Yeah. And so at that time I was like, Hey, I can't afford this, but I gotta figure out a way to make some money and, keep the mortgage paid. And I wasn't able to do that. Like I, I lost my home to foreclosure, went through bankruptcy, lost custody of my kids, and in that moment, that's where I had to go through my own transformation experience where. I had to reinvent myself because there was a time where I thought I was an Air Force member, right? Like, that's who I am. That's my identity. And so now I had to learn how to be a civilian because I joined the Air Force at 19, and I was still a kid in a knucklehead when I joined. And so I knew nothing about being a civilian as an adult. And so, you know, I had to one, learn how to be a civilian, but now I have to learn how to be a civilian as an adult, and then now I gotta, mm-hmm. How do I go out here and hunt because I've never had to hunt before. Because the Air Force literally first and 15th gave me a paycheck, right? And so one day I was out and about and I gave you all of that to kind of bring you to how I got started. Of course, now, one day I was, in the local community where I lived. Macon, Georgia. And I would just go to different, like community events or community activities. So if they had like a business networking event, you know, I would attend. Or if they had a small business week, I would attend. And one day I was having a conversation with a young lady and she basically asked me where was I from? And I said, I'm from Birmingham, Alabama. And she's like, no, you don't sound like you're from Birmingham. And I was like, no, I get it. I said, but I'm also, transitioning outta the Air Force. And she's like, ah, that's it. She's like, you don't, you definitely don't sound like you're from around here, and you definitely don't think like anybody around here. And so that was a huge shock for me because. I really didn't hang out with a lot of civilians because when you're, you know, when you're in a culture or a tribe Yeah. Community, you really associate right. With the people that, that you rock with. And so I didn't hang out with a lot of civilians. And so when she said this, I had like this kind of a mind blowing epiphany, moment where I was like, whoa, there's a huge difference between the way military members think and operate versus civilians. And so I saw that as an opportunity to be able to say, okay, there are people who, for lack of a better term, lack I guess, and no pun intended, that lack some things that I have. And I saw that as a way for me to be able to say, oh, okay, well, I've got some education, some training, some experience that I can take from my military time and then go into whether it's small businesses, nonprofits, or even government organizations. And serve and add value. And so that's really where, the birth of what I currently do was born, it started out leadership development, a little life coaching mixed in. And then I ran in, I went to a conference and I met a guy at this conference in 2016 and he started to talk about the importance of systems in your business. Mm-hmm. And I, mm-hmm. Stood the concept very well because air traffic control, which is what I did while in the military, is built on the system, right? Mm-hmm. So it's about safe and efficient flow of air traffic and everything is always about creating a plan that allows you to work within the parameters of the FAA, which is the Federal Aviation Administration to how to work within their system. And from a system, infrastructure. Blockchain, you know, kind of flow of things. I, I fully understood it. The problem I had though is I didn't know how to bring it all together from an online tech with workflows and automations and triggers and all the things. Yeah. And that was my journey, right? I dove headfirst into it. I had to figure it out. Made a lot of mistakes, lost a lot of money, to the tens of thousands of dollars and to the years. I also look at it as tuition paid. Like I had to go through those things, so that other people don't have to go through it. And kind of long put a button on that story. That's how I got here. That's how I got started. And that's literally how, you know why I love what I do. Is that enough chaos for you by the way? That Oh my God. That is like so much chaos. I was like, well, we don't even have to ask about chaos anymore. Look, hey, I grew up domestic violence, so that stepfather that I referred to earlier, we were a DV family, and so I, I get chaos. We moved every one to two years, and so there was no stability. I fully understand chaos. Mm-hmm. And so then to go, into the military and be able to, I don't say be able to. I guess it kinda look, depends on how you look at it. I never thought I'd go to countries like Baghdad or go to Africa, but unfortunately while there, you're in chaos, right? You're in war zone. And so, I think I've got my degree, uh, PhD in chaos, so I can definitely speak to it. You've definitely majored in it 100%. Oh my gosh. Okay. I love that you were talking about how you were figuring out with building the systems within the system. And because I had this one class, and I think that you might enjoy this, but like, I have this one class back in college. I'm a psych major, so I did 10 years, working in the mental health field. But before that, when I was in college, I took this one class, and this is one that was just simply for the like systems geeky girl inside me where I was just like. It was called like psychology and the visual eye. Okay. So it was all about how people perceive mm-hmm. The world around them. Mm-hmm. And how, like signs are made that automatically, like as we grew up, we learn what that means. We know what the yield sign means, we know what a stop sign means, even if it's just the red hexagon and not the word stop for sure. So like now part of when I help people write like playbooks and backend systems, I'm just like, oh, well yes, all your content is there, but your employees are not gonna understand this or their eyes are gonna gloss over because you're not visually making it appeasing to the brain. Mm-hmm. For sure. So I love that. I love now that I can make systems with psychology and the fact that you've taken what you've learned in your experience in the Air Force and, you know, going through the chaotic life that you've had so far is, that you are now in this position where you can help people not have as much chaos as you did. And our listeners, if you are, if you're counting, we've saved chaos like a gazillion times. This episode might end up being like a drinking game at one point. Let's do it. Let's do it. So. Let's take a quick little shift. Let's shift to if somebody is hearing your story and resonating with what you are saying, what's like a good, like first step, you know, if someone's like, okay, I'm hearing you, I think I'm ready to like, start moving my business to either free up some time, or, make it more impactful without the stress and the extra work. What's a good first step that you would suggest to them? Yeah. So the first thing is get clear on what you do want, right? Mm-hmm. Like what lifestyle do you want? For example, do you want to have more time in the evening to where you can be present, when your kids get home from school? Or are you a homeschool parent and you need to have a business to where during the day. You can actually, be present with your kids and be the instructor or educator that they need you to be. And then you operate your business in the evening. Are you the business owner who says, you know what, I don't have any kids at all. However, I do have a significant other, or I'm single, but this is the lifestyle that I want to live. This is how much money I want to make. This is the kind of place that I want to live in. This is the kind of car I want to drive. These are the kind of people that I want to work with. Just kind of put that, get that stuff out of your head and literally put it on paper, literally. And the reason being is because when we have so much clutter or chaos going on in our minds, it's impossible. Yeah. Wants to take the necessary actions that we need to take because that confused mind doesn't take action. Right. And you mm-hmm. Probably better understand it and can diagnose it better than I can as a psych major. At the end of the day, once we get it out of our head and we put it on paper, it comes to life. Right? Yeah. And I'm not. There's some spirituality aspects to it as well, right, in terms of getting it outta your head and putting it on paper. But at the end of the day, once you put it on paper and you've got that type of clarity, it's a lot easier for you to be able to, set your boundaries. And become non-negotiable about certain things. So, for example, I no longer, you know, associate with certain people, because it's outside of the new lifestyle. I want live or I no longer, attend certain events or go into certain environments because they're no longer supportive or conducive for this new lifestyle that I want to live. So the very first thing is just get clear on exactly what you want, because once you have that clarity, you know exactly what actions to take and what actions not to take. That is so good. I am a big fan of also physically writing like pen to paper too. I know some people will like. Put it on their notes and all that. And I don't know, for me personally, something about like, literally writing it out, really does, like you said, it has this like, kind of like spiritual like transformation that you're just closing. I know like, natalie Ellis calls it, closing the tabs in your head, I love that we all, I have, like, I'm looking at my computer as we record, and I'm like, I have like 20, 20 tabs open right now. Many, yeah, for sure. Yeah. Same here. Same here. Yeah. If you're an entrepreneur with, and you don't have 20 tabs open, yeah. You're doing something wrong. You're doing something wrong, or you're. So, right, you are like, you've won being an entrepreneur. Yeah, absolutely. And yeah, I think what you're saying is like a first step too, is a lot of people, you know have these like, oh, I want this, I want that. But if you don't write it down, if you don't see it, you know, how are you gonna make it come to life? Because eventually your brain will get so clustered that. This thing that you want is gonna get so pushed back that you're not gonna be able to see it anymore. So I'm not a theologian or a preacher or anything like that. Yeah, I maybe a couple times in, in a past life, but, there's something about specifically, there's a bible verse that's, Habakkuk two and two. And it says, write the vision, make it plain so that he who sees it can run with it. And I know there are a lot of times we hear, you know, scriptures like that and it's difficult for us to understand like, how do I practically apply this particular scripture to my life? And that's literally what we're talking about. Like you talked earlier about. The importance of when it comes to writing things down, there's a transformation that occurs. Mm-hmm. And so one of the things that I do, myself, and I teach this to my clients as well, is whatever your goals are, right? We're gonna start with the larger goal of, whatever it is you want to achieve in the next. 10 years. But then of course, as they say, how do you eat an elephant? One bite at a time. So we break that down into bite-sized chunks and we'll break it down to a granular level to where once we get to the daily activities that are necessary for you to achieve that ultimate 10 year goal, that's when we begin to say every single day, yes. Every single day, you're going to get up and you're going to write your goals down. And the reason why you do that is because what you begin to do is you begin to condition your mind to look for ways in order for you to achieve whatever those goals might be. And so once you do that, you basically activate your reticular activated system. And once you activate your reticular activated system, you begin to see, so for example, people have, probably seen, or I go out and I buy this white car. Well, before buying this white car, I never even saw white cars in that model before. And all of a sudden now I start to see the same yes, same model everywhere. And you're like, oh my God, I should have never got this car.'cause everyone's got it. They were always there. But because you didn't activate your reticular activator system until you actually purchased the car yourself, you didn't notice'em. Oh, it's so funny that you bring up the story. I literally, when I was pregnant, with my first kid, I was just like, oh, okay. Like I'm pregnant and then all of a sudden not counting, you know, being at the OB clinic, but all of a sudden out in public, I'm like, oh my God, there's like a million pregnant people in this, like in our town. And I'm like. Are we all gonna have babies at the same time? And I'm just like, I swear, like I maybe saw like one or two, pregnant women at Target and all of a sudden now I'm just like, every aisle I'm just like. Am I, you know, you start seeing it, right? Yeah. You know, not to, belittle or be demeaning at all, but those pregnant women were everywhere the entire time. Yeah. Yeah. You're totally right. It's like once you get something or like you've. You've zoned in on it. Mm-hmm. Then all of a sudden, that's all your brain starts seeing it everywhere. Like you said, they were always there. Always there. You just, your brain wasn't activated to it. So I don't wanna run out of time, do you wanna tell our listeners about your workshop that you, have. Yeah. Yeah. So, the work, less to Profit, more Masterclass. Right now we're doing them once per month. It's a two hour literally masterclass, a deep dive where I literally break down what we've, tailored as the catalyst system. It is specifically designed to help, online entrepreneurs who sell their knowledge just break free from the busy work. So that they can scale their business and enjoy more profits without them doing all of the work. And I think at the, again, it's just about creating, leverage, helping people create an asset, that generates revenue so that they can do the things that they love. It could be to, better support your church, your favorite charity to take care of family members to take care of kids in college. Or take your dream vacation earnest money for your dream home, or buy your dream car, what you know, whatever it is. Because we all have different desires based on where we are, you know, in our life journey. But at the end of the day, it's about helping you, just create an asset. So you don't have to worry about, Hey, when is my, where's my next client gonna come from? How do I generate leads? And then how do I, you know, get sales without being salesy, sleazy, or manipulative? And so I basically break down, the psychology and the strategy behind that, in an online context mm-hmm. So that people can make more money and have that time freedom. Awesome. Love that. So Jay, if someone is really resonating with everything that you're saying, how can they connect with you? Where can they find you on? I am on every single social media platform that you can think of. Maybe not Snapchat. But yeah. So Snapchat still exist? I think so. I don't know. I don't, oh my gosh. I haven't seen Snapchat forever. Yeah. On Facebook and, LinkedIn. You can just find me as Jay Jackson. Same thing on Instagram. So Jay Jackson on Instagram. My handle, though, on Instagram is at Disruptive Leaders Alliance. Because we're all about disruptive leadership. If you're on YouTube as well, I've got two YouTube channels, the Disruptive Leadership Podcast and j Jackson is business systems. Awesome. And listeners, as always, I will put all those, links and information down in our podcast notes so you can go grab them there. Obviously if you are driving, don't do that now, but definitely you want to connect, you can grab those links down below. So Jay J of course, we're wrapping up, so any closing thoughts you have for our listeners. Yeah, just no matter, two things. I guess, kind of two closing thoughts. No matter how good you think things are right now, at any moment they can become chaotic and I hope my story and sharing that with you earlier. Help you see that no one is safe, no matter what you are currently doing right now. And I think entrepreneurship gives you the best opportunity to have freedom to make decisions that you wanna make with your life. Mm-hmm. So, be proactive, you know, set yourself up, create some systems or a side hustle or, you know, go all in on your side hustle, so that no one can come in and disrupt your life. So that's. Part one or first thought. And my second thought is if you are currently in the chaos, right? If you're currently pulling your hair out, going through a divorce, fired from a job, the death you know of a family member that you love, just trust and believe that everything is always going to be okay. There's a cliche out there and I. Say it's a cliche because people kind of toss it around with without, I don't think understanding it. Mm-hmm. But that cliche is that the universe has your back or, you know, everything is working out for your good. Mm-hmm. And I truly believe that to be the case. I've had several experiences in my life. I've talked to you about domestic violence growing up. I talked to you about being let go from my, what I. Thought was my career, but realize now it's just a job. Yeah. And I even almost my daughter almost died during Covid where she had to be put on a ventilator. So I'm saying these things from a place of experience. When I say that no matter what you're going through, no matter how chaotic it might feel, no matter how deep you might think you're in a hole. Again, having been through BAS and foreclosure, I promise you there are brighter days and things will improve. Prove. You just have to maintain that belief and that faith, and just continue to work towards what you put on paper, in terms of what you said that you want that future life to be like. And if you do that, I promise you, I can guarantee you, that you will turn things around and you'll experience a transformation. Oh my gosh, those are so good. Maybe you should be a preacher. So, so, uh, context. I did try it for a year. Of course. No, no, no. Seriously, seriously. Like, so we do have a ministry. Where every week, and it's on Thursdays. Today was the day that, we've got a couple of volunteers who go pick up the food for us and they drop it off. And we only feed senior communities that are fi 55 plus. But we've got a couple of volunteers that does that for us every single week. But it started with me actually being a pastor. Oh, wow. And. I still believe that my calling is ministry and to serve and help people, and that's why we still do the food ministry component. Mm-hmm. But I stepped away from the platform or the pulpit because I realized that the transformation that I personally have experienced and the level of understanding. And or belief in faith and what? I believe in terms of certain words that I've read in terms of scripture, and I believe these things because of practically applying them to my life. Yeah. So I know that they work. I realized that in order for me to have the maximum impact, it could not be in the context of a church because the church and religion, puts you in a box. Right. That's fair. Yeah. The expectation is that you behave a certain way, dress a certain way, talk a certain way, think a certain way. And I was just like, you're not gonna get me to certain way do anything. And so, we slowly pulled out of it. But yet again, we still serve, we still have our ministry and we still give back. So yeah, that's where my ability to kinda, do an inspirational or pull a scripture out. That's where that comes from. Yeah, I think it works. I think that having all that past experience and then now hearing you speak and talking with you through this podcast is like, I can see how you can inspire people and I get that feeling straight off the bat from you. Okay. And the fact that you are just so open and, you know, basically told our listeners so much.'cause I think that your story. And what you've gone through will resonate with our listeners and people will be seen because you've gone through so much that anyone who's gone through any type of ordeal like you have. They're like, oh, okay. Well, yeah, I get Jay, you know, I was that person too. And so I think your story makes a lot of people seen because of how much you've gone through. And so I really appreciate you coming and sharing that with us. Yeah, my pleasure, man. That's, I mean, that's why we do the work that we do. That's why you do what you do, right. To mm-hmm. Bring in people who can share their stories and their testimonies to be able to, free or release other people from whatever they might be going through, or to help them kind of navigate the landmines of life or business. So, that's why we do the work that we do, and I love it. Awesome. Okay, so we will have to like, have you back and catch up and I'm sure you'll come back with like, Whitney, I have five more chaotic stories for you. Yeah. Oh, trust me, I, look, I just went on a small little pouch today, right? Like I've got a dump bag over here with chaos. I promise you. Okay, next time. Next time, bring all the luggage. All right. I'll bring it all, not just to carry on. Yeah, trust me, I got tons of baggage that I can bring with me. No, for sure. For sure. Well, thank you again for coming on the podcast and listeners, I will see you all in the next one. That's a wrap on another episode of Caffeinated Chaos. I hope you're leaving with a little more clarity, a lot more inspiration, and maybe even an extra shot of motivation. If you love today's episode, don't forget to follow us. Leave a review and share it with a friend who could use just a little chaos and caffeine in their life. Until next time, keep embracing the mess. Chase your dreams and make magic happen. One caffeinated, chaotic moment at a time. I will see you all soon. Bye now.

People on this episode

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Whitney Mihalko - Aguon

Host
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Jay Jackson

Guest

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